1: With sulfuric acid; sodium nitrite in water T=5°C; 1 h; 2: With potassium iodide in water T=5 - 20°C;

2-[(dimethylamino)methyl]-1-thiophenolato-copper(I); caesium carbonate in dimethyl sulfoxide T=160°C; 16 h; Inert atmosphere; chemoselective reaction;

1.1: 93 percent / K2CO3 / dimethylsulfoxide / 4 h / 120 °C 2.1: 69 percent / tin; HCl; water / 2 h / 50 °C 3.1: H2SO4; NaNO2 / H2O / 1 h / 5 °C 3.2: 60 percent / potassium iodide / H2O / 5 - 20 °C View Scheme

1.1: 69 percent / tin; HCl; water / 2 h / 50 °C 2.1: H2SO4; NaNO2 / H2O / 1 h / 5 °C 2.2: 60 percent / potassium iodide / H2O / 5 - 20 °C View Scheme

1.1: 93 percent / K2CO3 / dimethylsulfoxide / 4 h / 120 °C 2.1: 69 percent / tin; HCl; water / 2 h / 50 °C 3.1: H2SO4; NaNO2 / H2O / 1 h / 5 °C 3.2: 60 percent / potassium iodide / H2O / 5 - 20 °C View Scheme